Ryan Is Damned if He Does, and Damned if He Doesn’t

by Stuart RothenbergOctober 18, 2015 · 9:30 AM EDT

I first met the Wisconsin Republican when he came in for an interview on Nov. 19, 1997. Then 27, he most recently had been a Capitol Hill staffer for conservative Kansas Sen. Sam Brownback.

Ryan was making his first run for office in a politically competitive district in southeastern Wisconsin. I don’t remember anything about the questions I asked him or about Ryan’s responses (my notes didn’t survive), but I do recall that after the session ended, as we were shaking hands prior to his departure, Ryan did something that candidates almost never do — he asked how he had done in the interview.

Candidates don’t ask, I suppose, because it is an awkward question that could produce a discouraging answer. But Ryan wasn’t your typical candidate. He was much younger than most and full of enthusiasm, with a naiveté I found appealing.

I told him with complete honesty that he did very well. I said it was clear that he was interested in policy and knew a lot about the issues, but he also had a good understanding of politics. I told him I found him personable and likable.

And then I told him I expected him to lose, go into the private sector, make some good money and run for office again, this time successfully. I told him he had a bright future, but this probably was not his race.

For me, that assessment, made off the top of my head many months before the Republican primary, let alone the general election, was not a hard call. Ryan was very young and looked it. He had never raised money. He had never run for office.

The congressional district certainly was competitive, but it leaned Democratic. Democrat Mike Dukakis narrowly won there in the 1988 presidential contest and Bill Clinton carried it twice, in both 1992 and 1996.

The sitting congressman, Republican Mark Neumann, barely beat Kenosha City Council President Lydia Spottswood, a Democrat, 51 percent to 49 percent, in 1996 to win a second term. Now Neumann was running for the Senate. Spottswood, a nurse by profession, was back for another try in 1998, and given her past performance and experience, she looked like the favorite.

Although I told Ryan after our meeting that I expected him to lose, that is not how I rated the race. In the Rothenberg Political Report House Overview dated Jan. 23, 1998, I classified the open-seat contest as a Tossup, but added that Spottswood began with the edge. I reiterated that Pure Tossup rating in a May 15, 1998, issue.

An in-depth view of the Ryan-Spottswood race appeared in the June 26, 1998, issue of my newsletter, a little more than four months before Election Day. After profiling the two candidates and discussing their campaigns, I noted that one longtime observer believed Democrats had the upper hand in the race because they had an experienced candidate who barely lost last time and now had a unified party behind her. I then wrote:

"But Ryan’s high energy, non-stop early efforts may well have scared off candidates with more credentials, and the youthful Republican has put together an impressive list of names on his steering committee, suggesting that he knows how to put together a campaign. The lack of a big-name Republican in the race, then, may say something about Ryan’s early efforts."

I concluded: “Wisconsin 1 remains an excellent takeover opportunity for Democrats, and it is clearly the kind of contest they must win if they are to gain seats or even takeover the House. It’s too soon to give either candidate a decisive advantage.”

Ryan won the GOP nomination in an early September primary, and it wasn’t long before I started hearing that Spottswoood wasn’t running a great race, while Ryan was working hard and impressing voters, even in Democratic areas.

Though I had expected Spottswood would open up a lead, that never happened. And because of that, my newsletter never moved the Spottswood-Ryan race out of the Tossup category. The contest appeared too close to call all the way to November.

Ryan won that election, by a surprisingly wide 14-point margin, 57.1 percent to 42.7 percent, and the outcome — a comfortable victory in a swing district against an experienced Democratic opponent — surely was testament to his energy and intellect.

Now, Paul Ryan is faced with a difficult choice. Does he turn a deaf ear to those Republicans, from John A. Boehner to Mitt Romney, who are urging him to run for speaker, or does he accept the challenge, knowing that the job may be impossible?

Ryan has become a significant player on Capitol Hill, and not primarily because Mitt Romney chose him to be the GOP nominee for vice president in 2012. The congressman is thoughtful and analytic, but he is also consistently conservative. He is the one person who might hold House Republicans together. But for how long?

Eventually, issues like the debt ceiling and appropriations will have to be addressed again, and the party’s Freedom Caucus (and other conservatives unwilling to compromise) will make demands that the White House and Democrats will not accept, putting the speaker in a no-win position.

Ryan’s intellect, sincerity and savvy may help him avoid a bump or two initially, but it’s unclear that anyone can lead House Republicans right now. Because of that, those who admire him have reason to worry if he ultimately puts his party over his career as a legislator.